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16.13.4.1.4.4.3 Variation 3: Alkoxy, Aryloxy, Alkylsulfanyl, and Arylsulfanyl Group Transformations

DOI: 10.1055/sos-SD-016-00745

Kikelj, D.Science of Synthesis, (200416705.

Quinazolin-4-amines 278 and quinazolin-2-amines 280 are conveniently obtained by nucleophilic displacement of 4- and/or 2-alkoxy,[‌288‌,‌804‌,‌822‌,‌834‌,‌835‌] aryloxy,[‌804‌,‌836‌,‌837‌] alkylsulfanyl,[‌508‌,‌800‌,‌804‌,‌805‌,‌813‌‌815‌,‌838‌] or arylsulfanyl[‌325‌,‌839‌] groups in the quinazolines 277 and 279 with amines (Scheme 211). These groups are displaced also by hydrazine[‌288‌,‌805‌,‌813‌] or hydroxylamines.[‌813‌] Quinazolin-4-yl ethers and thioethers are generally more reactive toward nucleophilic substitution than the corresponding 2-isomers. 4-Alkoxyquinazolines undergo transetherification on heating with alcoholic sodium alkoxide solution.[‌835‌,‌840‌]

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References


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